Hydrochloric Acid → HCID 59563488, compound

HRID 467946Notes

Reaction equation

HRID 467946 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)=[CH:6][C:5]=1[CH3:28].[OH-].[K+].Cl>O1CCCC1.CO.O>[Br:10][C:8]1[C:7]([C:11]2[CH2:15][C:14]([C:20]3[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=3)([C:16]([F:18])([F:19])[F:17])[O:13][N:12]=2)=[CH:6][C:5]([CH3:28])=[C:4]([CH:9]=1)[C:3]([OH:29])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59563499HCID 59563499, compound

Product 1

HCID 59563488HCID 59563488, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester (Example I22) (290 mg) in tetrahydrofuran (3 ml) was added a solution of potassium hydroxide (1.53 g) in methanol (3 ml) and water (3 ml). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was acidified by addition of aqueous hydrochloric acid (4N). The aqueous phase was extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with water (3×10 ml) and brine, dried over sodium sulfate, and concentrated to afford 5-bromo-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (220 mg) as a white foam. 1H-NMR (CDCl3, 400 MHz): 8.20 (s, 1H), 7.30-7.50 (m, 4H), 4.20 (d, 1H), 3.80 (d, 1H), 2.50 (s, 3H).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×10 ml)
  2. washThe combined organic extracts were washed with water (3×10 ml) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-44bdbe37b88e44fdbf0682ccde769396
Source dataset
uspto-grants-2014_01
Patent number
US08623896B2

Reaction notes

Loading…